The gist of it is that he is kinda shit at combat yes, but anywhere he send his gang to will become a brutal battlefield/major crisis point despite it always seems to be innocuous. They happened so frequently and the battle are always so over the top that those in the know dubbed it "Thousands Trials" due to how difficult his tasks are. It's some kind of weird luck on his part but to those look from outside it look likes he is some kind of omniscience deity who is like "Everything is exactly as I machinated"
It's also why his gang are adamant about him staying with them, mostly because they thought his wisdom and foresight is so far beyond them that it seem godly even.
Basically it usually went like: Cry say weird vague shits, send people to some butt nowhere with bare information-> butt nowhere turn out to be ultra difficult -> shit resolved, everyone thought he planned this all along.